On the mechanism of unexpected potentiometric response to neutral phenols by liquid membranes based on quaternary ammonium salts - Systematic experimental and theoretical approaches

Journal of the American Chemical Society

Volumn 120, Issue 13, 1998, Pages 3049-3059

  Ito, Takashi ^a   Radecka, Hanna ^b,c   Tohda, Koji ^a   Odashima, Kazunori ^a   Umezawa, Yoshio ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c UNIV OF AGRICULTURE AND TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE; PHOSPHONIUM DERIVATIVE; POLYVINYLCHLORIDE; QUATERNARY AMMONIUM DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; ION SELECTIVE ELECTRODE; LIQUID MEMBRANE; MEMBRANE POTENTIAL; PHASE TRANSITION; POTENTIOMETRY; PROTON TRANSPORT; SENSOR;

EID: 0032495780     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973179v     Document Type: Article

References (70)

1. (a) CRC Handbook of Ion-Selective Electrodes: Selectivity Coefficients; Umezawa, Y., Ed.; CRC Press: Boca Raton, FL, 1990.
2. (b) Brzózka, Z. In Supramolecular Technology; Reinhoudt, D. N., Ed.; Comprehensive Supramolecular Chemistry 10; Elsevier Science: Oxford, U.K., 1996; Chapter 8 (pp 187-212).
3. (c) Bakker, E.; Bühlmann, P.; Pretsch, E. Chem. Rev. 1997, 97, 3083-3132.
4. (d) Bühlmann, P.; Pretsch, E.; Bakker, E. Submitted for publication.
5. (e) Odashima, K. J. Inclusion Phenom. Mol. Recognit. Chem. 1998, in press.
6. (a) Eisenman, G. Ion-Selective Electrodes; Durst, R. A., Ed.; Special Publication 314; National Bureau of Standards: Washington, D.C., 1969; Chapter 1, pp 1-56.
7. (b) Buck, R. P. In Ion-Selective Electrodes in Analytical Chemistry; Freiser, H., Ed.; Plenum Press: New York, 1978; Vol 1, pp 1-141.
8. (c) Morf, W. E. The Principle of Ion-Selective Electrodes and of Membrane Transport; Elsevier: Amsterdam, 1981.
9. (d) Lindner, E.; Tóth, K.; Pungor, E. Dynamic Characterization of Ion-Selective Electrodes; CRC Press: Boca Raton, FL, 1988.
10. (a) Morf, W. E.; Wuhrmann, P.; Simon, W. Anal. Chem. 1976, 48, 1031-1039
11. (b) Thoma, A. P.; Viviani-Nauer, A.; Arranitis, S.; Morf, W. E.; Simon, W. Anal. Chem. 1977, 49, 1567-1572.
12. (c) Fiedler, U. Anal. Chim. Acta 1977, 89, 101-109.
13. (d) Morf, W. E.; Simon, W. Helv. Chim. Acta 1986, 69, 1120-1131.
14. (a) Craggs, A.; Moody, G. J.; Thomas, J. D. R. Talanta 1976, 23, 799-804.
15. (b) Jaber, A. M. Y.; Moody, G. J.; Thomas, J. D. R. Talanta 1977, 24, 655-657.
16. (c) Doyle, B.; Moody, G. J.; Thomas, J. D. R. Talanta 1982, 29, 257-262.
17. (d) Doyle, B.; Moody, G. J.; Thomas, J. D. R. Talanta 1982, 29, 609-614.
18. Tohda, K.; Yoshiyagawa, S.; Kataoka, M.; Odashima, K.; Umezawa, Y. Anal. Chem. 1997, 69, 3360-3369. This paper describes experimental confirmation of a theoretical response model based on a local phase boundary equilibrium condition, in which surface charge density was quantitatively correlated with respective charged species involved in the phase boundary equilibrium.
19. (a) Kellner, R.; Fischbock, G.; Götzinger, G.; Pungor, E.; Tóth, K.; Polos, E.; Lindner, E. Fresenius' Z. Anal. Chem. 1985, 322, 151-156.
20. (b) Kellner, R.; Zippel, E.; Pungor, E.; Tóth, K.; Lindner, E. Fresenius' Z. Anal. Chem. 1987, 328, 464-468.
21. (c) Tóth, K.; Lindner, E.; Pungor, E.; Zippel, E.; Kellner, R. Fresenius' Z. Anal. Chem. 1988, 331, 448-453.
22. (d) Umezawa, K.; Lin, X.; Nishizawa, S.; Sugawara, M.; Umezawa, Y. Anal. Chim. Acta 1993, 282, 247-257.
23. (e) Tohda, K.; Umezawa, Y.; Yoshiyagawa, S.; Hashimoto, S.; Kawasaki, M. Anal. Chem. 1995, 67, 570-577.
24. (f) Bühlmann, P.; Yajima, S.; Tohda, K.; Umezawa, K.; Nishizawa, S.; Umezawa, Y. Electroanalysis 1995, 7, 811-816.
25. (g) Yajima, S.; Tohda, K.; Bühlmann, P.; Umezawa, Y. Anal. Chem. 1997, 69, 1919-1924.
26. (a) Jones, D. L.; Moody, G. J.; Thomas, J. D. R. Analyst 1981, 106, 439-447.
27. (b) Jones, D. L.; Moody, G. J.; Thomas, J. D. R.; Birch, B. J. Analyst 1981, 106, 974-984.
28. (c) Sugawara, M.; Nagasawa, S.; Ohashi, N. J. Electroanal. Chem. 1984, 176, 183-194.
29. (d) Kojima, K.; Sugawara, M.; Umezawa, Y. Anal. Sci. 1985, 1, 477-478.
30. (e) Anzai, J.; Liu, C. Sens. Actuators B 1991, 5, 171-172.
31. (f) Espadas-Torre, C.; Bakker, E.; Barker, S.; Meyerhoff, M. E. Anal. Chem. 1996, 68, 1623-1631.
32. -1 and a selectivity for p-nitrophenol. The response and selectivity of these membranes were interpreted by partition of the phenolic compounds into the membrane and its complexation with the anionic component of the ammonium salt.
33. Kurihara, K.; Ohto, K.; Tanaka, Y.; Aoyama, Y.; Kunitake, T. J. Am. Chem. Soc. 1991, 113, 444-450.
34. Kurihara, K. Jpn. J. Physiol. 1990, 40, 305-324.
35. Kimura, E.; Watanabe, A.; Kodama, M. J. Am. Chem. Soc. 1983, 105, 2063-2066.
36. (a) Umezawa, Y.; Sugawara, M.; Kataoka, M.; Odashima, K. In Ion-Selective Electrodes: Pungor, E., Ed.; Akadémiai Kiadó (Pergamon Press): Budapest (Oxford), 1989; Vol 5, pp 211-234.
37. (b) Odashima, K.; Umezawa, Y. In Biosensor Technology. Fundamentals and Applications; Buck, R. P., Hatfield, W. E., Umaña, M., Bowden, E. F., Eds.; Marcel Dekker: New York, 1990; pp 71-93.
38. Ito, T.; Radecka, H.; Umezawa, K.; Kimura, T.; Kataoka, M.; Yashiro, A.; Lin, X. M.; Kimura, E.; Sessler, J. L.; Odashima, K.; Umezawa, Y. Anal. Sci. 1998, 14, 89-98.
39. Ito, T.; Tohda, K.; Odashima, K.; Umezawa, Y. To be submitted for publication.
40. Tohda, K.; Tange, M.; Odashima, K.; Umezawa, Y.; Furuta, H.; Sessler, J. L. Anal. Chem. 1992, 64, 960-964.
41. (a) Uemasu, I.; Umezawa, Y. Anal. Chem. 1982, 54, 1198-1200.
42. (b) Lindner, E.; Tóth, K.; Pungor, E.; Umezawa, Y. Anal. Chem. 1984, 56, 808-810.
43. (c) Lindner, E.; Tóth, K.; Pungor, E. Pure Appl. Chem. 1986, 58, 469-479.
44. 1 in Figure 7b), because the condition ΔE/Δt < 0.4 was satisfied at this point. See footnote 22.
45. (a) Gadzekpo, V. P. Y.; Christian, G. D. Anal. Chim. Acta 1984, 164, 279-282.
46. (b) Umezawa, Y.; Umezawa, K.; Sato, H. Pure Appl. Chem. 1995, 67, 507-518.
47. Dean, J. A. Lange's Handbook of Chemistry, 14 ed.; McGraw-Hill: New York, 1992; pp 8.19-8.71.
48. Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525-616.
49. -4 M).
50. -2 M MES buffer.
51. (b) Seemingly very small pH effect observed in Figures 4 and 5 does not contradict the pH dependence demonstrated by Figure 6 (parts a and b), because, in the former cases, the contribution of each anion to the charge separation could be different at different pH's.
52. 7f
53. (a) Relles, H. M. J. Org. Chem. 1970, 35, 4280-4282.
54. (b) Taylor, R. P.; Kuntz, I. D., Jr. J. Phys. Chem. 1970, 74, 4573-4577.
55. (c) Bacelon, P.; Corset, J.; De Loze, C. Chem. Phys. Lett. 1975, 32, 458-461.
56. (d) Rulinda, J. B.; Zeegers-Huyskens, T. Spectroscopy Lett. 1979, 12, 33-43.
57. (e) Bunton, C. A.; Cowell, C. P. J. Colloid Interface Sci. 1988, 122, 154-161.
58. (a) Sawada, K.; Sohara, T.; Kikuchi, Y. J. Chem. Soc., Faraday Trans. 1995, 91, 643-647.
59. (b) Millero, F. J. Chem. Rev. 1971, 71, 147-176.
60. Enhanced extraction of 12 in an aqueous solution (pH 4-5) by a solution of 2 in benzene or cyclohexane has been previously reported (Inoue, K.; Shishido, H. Solvent Ext. Ion Exch. 1986, 4, 199-216). However, no description is found for the change in the pH of the aqueous phase.
61. 4 (pH 4.0).
62. 27c (a) Kohara, H. Japan Analyst 1968, 17, 1147-1148. (b) Mukerjee, P.; Banerjee, K. J. Phys. Chem. 1964, 68, 3567-3574. (c) Kimura, E.; Sakonaka, A.; Kodama, M. J. Am. Chem. Soc. 1982, 104, 4984-4985.
63. 27c (a) Kohara, H. Japan Analyst 1968, 17, 1147-1148. (b) Mukerjee, P.; Banerjee, K. J. Phys. Chem. 1964, 68, 3567-3574. (c) Kimura, E.; Sakonaka, A.; Kodama, M. J. Am. Chem. Soc. 1982, 104, 4984-4985.
64. 27c (a) Kohara, H. Japan Analyst 1968, 17, 1147-1148. (b) Mukerjee, P.; Banerjee, K. J. Phys. Chem. 1964, 68, 3567-3574. (c) Kimura, E.; Sakonaka, A.; Kodama, M. J. Am. Chem. Soc. 1982, 104, 4984-4985.
65. - ion.
66. Based on a different model focused on kinetic processes, Meyerhoff et al. also explained the super-Nernstian anionic response to polyanion heparin by a PVC matrix liquid membrane based on quaternary ammonium salt 3a (Fu, B.; Bakker, E.; Yang, J. H.; Meyerhoff, M. E. Anal. Chem. 1994, 66, 2250-2259).
67. Corn, R. M.; Higgins, D. A. Chem. Rev. 1994, 94, 107-125.
68. The time profile of SHG, concerning with only the interface of the membrane and the sample solution, did not show a gradual increase after the initial decrease in contrast to the potential vs time curve shown in Figure 7a (see footnote 22).
69. 32a,b interface. (a) Bell, A. J.; Frey, J. G.; VanderNoot, T. J. J. Chem. Soc., Faraday Trans. 1992, 88, 2027-2030. (b) Sarkar, N.; Das, K.; Das, S.; Nath, D.; Bhattacharyya, K. J. Chem. Soc., Faraday Trans. 1995, 91, 1769-1773.
70. 32a,b interface. (a) Bell, A. J.; Frey, J. G.; VanderNoot, T. J. J. Chem. Soc., Faraday Trans. 1992, 88, 2027-2030. (b) Sarkar, N.; Das, K.; Das, S.; Nath, D.; Bhattacharyya, K. J. Chem. Soc., Faraday Trans. 1995, 91, 1769-1773.